1-(2,2,2,-Trichloroethoxycarbonyl)-3-(RS)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidine → Methyl 4-(thiophen-3-yl)pyrrolidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.1 g (2.9 mmol) of 1-(2,2,2,-trichloroethoxycarbonyl)-3-(SR)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidine in 30 mL of acetic acid at 40° C. was slowly added 0.5 g (7.6 mmol) of Zn powder and the reaction mixture was stirred a further 4 h at 40° C. The reaction mixture was filtered to remove the solid and the filter was washed with MeOH. The organic fraction was concentrated and the residue was purified by chomatography. (silica, CH2Cl9: MeOH: NH3 (2M in MeOH),100:4:2) to give 0.61 g of the title compound. 1H NMR (CDCl3) δ2.92 (m, 1H). 3.02 (m, 1H), 3.29 (m, 2H), 3.48-3.62 (m, 2H), 3.72 (s, 3H), 6.99 (d, 1H, J=5 HZ), 7.05 (s, 1H), 7.31 (m, 1H);

Provenance & Evidence